221 Trails in Massachusetts

Rank Trail Name Difficulty Length (mi) Rating City
51. Dogtown Advanced difficulty 15.0 ***** Gloucester
52. Chebacco Woods Intermediate difficulty 10.0 ***** Hamilton
53. Hale Reservation Beginner difficulty 10.0 **** Westwood
54. Hopkinton State Park Intermediate difficulty 10.0 **** Hopkinton
55. Georgetown-rowley State Forest Intermediate difficulty 9.0 **** Georgetown
56. Pearl Hill State Park Beginner difficulty 20.0 **** Townsend
57. Franklin State Forest Intermediate difficulty 7.0 **** Franklin State Forest
58. Carolina Hill Intermediate difficulty 10.0 **** Marshfield
59. Dubuque State Forest Advanced difficulty 16.0 ***** Hawley
60. Ice Houce (Sawmill Hills Conservation Area) Advanced difficulty 15 ***** Florence
61. West Hill Dam Intermediate difficulty 5.0 **** Upton
62. Bald Hill Reservation Beginner difficulty 10.0 *** Boxford
63. Granville Gorge Intermediate difficulty 8.0 ***** Granville
64. Ward Reservation Intermediate difficulty 12.0 ***** Andover
65. Nickerson State Park Beginner difficulty 20.0 *** Brewster
66. Ashland State Park Intermediate difficulty 7.0 *** Ashland
67. Groton Town Forest Beginner difficulty 6.0 *** Leominster
68. Willow Street Trails Intermediate difficulty 15.0 **** Yarmouth
69. Prospect Hill Beginner difficulty 10.0 **** Waltham
70. Freetown State Forest (Bent Rim Trail) Intermediate difficulty 4.0 *** Freetown
71. Mt toby Intermediate difficulty 16.0 ***** Sunderland
72. Upton State Forest Beginner difficulty 12.0 *** Upton
73. Beverly Commons Advanced difficulty 10 **** Beverly
74. Rutland State Forest Beginner difficulty 6.0 *** Rutland
75. Bradley Palmer Beginner difficulty 11.0 *** Topsfield
76. Ames Nowell Intermediate difficulty 10.0 *** Abington
77. Grafton Land Trust Intermediate difficulty 20.0 *** Grafton
78. Mendon Town Forest Intermediate difficulty 7.0 **** Mendon
79. DAR Advanced difficulty 16.0 **** Goshen
80. Oak Hill Advanced difficulty 8.0 **** Littleton
81. Myles Standish Forest Beginner difficulty 100.0 *** Plymouth
82. Rocky Mountain And Highland Park Beginner difficulty 30.0 *** Greenfield
83. Beaver Brook North Intermediate difficulty 4.0 **** Belmont
84. Charles River Loop Easiest difficulty 15 ** Boston
85. Maudslay State Park Intermediate difficulty 4.0 *** Newburyport
86. Vaughn Hill/bower Spring Trail System(s) Advanced difficulty 4.0 **** Bolton/harvard
87. Red Zone (Charlemont trails) Advanced difficulty 3.0 ***** Charlemont
88. Sutton Water Works Intermediate difficulty 5.0 **** Sutton
89. Holyoke Range Trails Intermediate difficulty 15.0 **** Amherst
90. Bachelor Street Trails Advanced difficulty 15.0 ***** Granby
91. Manhan Rail Trail difficulty 10.0 ***** Easthampton
92. Middle Distance Trail Intermediate difficulty 5.0 **** Deerfield
93. Merrimack River Trail Beginner difficulty 10.0 **** Andover
94. Henry S. Hunnewell Town Forest Intermediate difficulty 1.0 ***** Natick
95. Wma Trail Beginner difficulty 3.0 ***** Wilbraham
96. E-stranged Moose Intermediate difficulty 2.0 **** Charlemont
97. Caryl Park Beginner difficulty 17.0 *** Dover
98. Boynton Park Intermediate difficulty 3.0 *** Worcester
99. Nobscot Mtn. Intermediate difficulty 15.0 *** Sudbury
100. Facing Rocks Intermediate difficulty 7.0 *** Ludlow

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